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This week, the American Institute of Architects (AIA) unveils its latest Guide to New York, the must-have architectural bible that tracks -- block by block -- the city's significant structures. To celebrate the book's release (it's been a decade since the last update!), we combed through its 1,000-plus pages to come up with our own guide...to the city's 10 homeliest buildings.

A word about our unscientific methods: To keep things perfectly arbitrary, we stuck to 20th and 21st century architecture, while looking for the perfect combination of gaudy color palettes, cheap materials, and bloated/lazy/oppressive design. Naturally, we have buildings of all functions from all five boroughs, all of which figure in the newest edition of the AIA Guide to New York. And, naturally, this means that lots of hideousness got left on the cutting room floor. Never fear, architects and developers: we still adore you for your congeniality.

Without further ado, and in no particular order, our list of the New York skyline's gnarliest barnacles (the numbers each match the respective photo in the slideshow at bottom):

1. PALAZZO CHUPI, West Village (2007). This Curbed.com whipping boy -- designed by grandiloquent artist/film director Julian Schnabel -- is a muddle of Mediterranean styles rendered infinitely more unattractive by an exterior color palette that appears to have been inspired by a box of feminine care products. Don't believe me? Here's what the AIA has to say: "This 12-story eruption is a mess of competing balconies, arched windows, faux-Venetian details, and hot pink stucco. At a smaller scale, it might be funny, but it's too big to be a good joke." Especially if you live next door.

2. CO-OP CITY, Bronx (1968-1970). The single largest residential development in the U.S. was inspired by iconic architect Le Corbusier's 1920s plan to build a modern city that could accommodate three million people and lots of cars. But what might look good on a maquette, doesn't always work in real life. In this case, the buildings are dour, the public spaces, a chore to walk through and, overall, the design and materials have not aged well. The AIA describes them as a "non-environment, largely designed by bureaucrats with not a scintilla of wit." Unfortunately, New York is riddled with structures just like these.

3. WESTIN NEW YORK, Times Square (2002). Like a lady who leaves the house wearing every last piece of her costume jewelry, this unfortunate building -- designed by the Miami firm Arquitectonica -- is a hot mess of horizontal and vertical lines, odd angles and garish colors. "Histrionic" and "sadly banal," is how the AIA puts it. Ultimately, it's the sort of urban renewal project that could make one nostalgic for the Times Square of hookers and porn palaces.

4. WOODHULL MEDICAL CENTER, Bushwick (1977). If this were a factory churning out motor oil, I might consider this modern building well-designed. But it's a hospital, a place where the wounded and the sick go to heal. And the sulking exterior and massive scale do little to inspire that. (Unless being terrorized into getting better counts.) There is a mitigating factor: Woodhull lets uninsured area artists swap services for health care.

5. HEARST TOWER, Columbus Circle Area (1927-28 and 2006). On their own, each of the structures that comprise this unusual pairing are attractive. But, together, not so much. The structure consists of a zig-zagging, contemporary tower, designed by British starchitect Norman Foster, that emerges from the shell of a 1920s deco building -- an architectural juxtaposition that led the AIA's writers to draw a comparison to the belly-bursting monsters on Aliens. Not good.

6. WATERSIDE PLAZA, Kips Bay (1974). Brutal to the point of looking Soviet, these residential structures on the east side of Manhattan are worthy of being cast in some dystopic sci-fi flick à la Gattaca. Moreover, they're completely disconnected from the rest of the city by the elevated rush of traffic on the FDR. The over-all effect: off-putting.

7. SOCIETY OF ST. PAUL SEMINARY, Staten Island (1969). Sometimes ugly can be charming -- as is the case for this flamboyant building. Flourishes include slanted windows and some unusual floating staircases on the roof, details that have earned it the AIA honorrfic of "Staten Island's most bizarre building." Yes, it's ugly, but we love it -- in the same way we love dogs that look like this.

8. CITYLIGHTS, Long Island City (1998). More bland than ugly, it's probably unfair to pick on this tower designed by Cesar Pelli (the architect behind the MoMA-adjacent Museum Tower). But its total boringness is symbolic of all the tedious condos that have cluttered the city's skyline since the late '90s (think: the East River waterfront, McCarren Park, much of the west side of Manhattan, anything Trump). Worse: the tower feels disconnected from the neighborhood around it, a purgatory for pedestrians approaching from the east.

9. WHITNEY MUSEUM OF ART, Upper East Side (1963-66). Marcel Breuer's bunker/museum is historic, important and, in its day, seriously avant garde. The AIA describes it as a "must-be-seen modern object." But that doesn't make it pretty.

10. METROTECH CENTER, Downtown Brooklyn (from 1989). This 11-block development at Flatbush and Tillary is an architectural mixed bag -- some of it interesting (Davis Brody Bond's sleek Othmer Residence Hall), much of it a snore (15 Metro Tech Center). Walking through this dull morass can be soul-crushing. But the real problem here, says the AIA, is the way in which one company appropriated a vast swath of public space and made it into their own quasi-private territory, complete with battalions of security guards. The complex should serve as a lesson on letting developers and architects build monuments to themselves, with little consideration for how these projects might weave into the greater urban fabric. It may be a lesson we have yet to learn. Metrotech's developer, Forest City Ratner, is now working on another behemoth 22-acre project nearby: the highly controversial Atlantic Yards.

Do you have some architectural heinousness of your own that you would like to share? Submit photos to our Flickr pool. We'll feature the ten best -- er, ugliest -- ones in a slideshow on this site next week.

Add 25-18 Union St. in Flushing to this list...I lived there decades ago, when it facade was nearly perfect. Now its exterior as found 2 weeks ago through Google Maps conjures up semi-slum associations, which is all the more bizarre given that the gardens surrounding it seem top notch and certainly an upgrade from the reality of the 1970's.A part in me refuses to believe that those in charge have allowed the building to become that ugly.

Oddly, I used to think the AIG building on West Side Hwy was the ugliest but for some reason or another, it has grown on me. Perhaps because of the building being put up next to it?What baffles me is "The O'toole" building on 7th (St. Vincents, what used to be, Hospital). I understand that it is significant, for what? remains a mystery to me. It is an eyesore, through and through. If they were after a replica of the Maritime Building, they were way off.I also would add the Trump Town fiasco on the West Side Hwy. All of those brown colored yuck huts, bunched together... Oh and throw in The Trump on 5th Avenue or anything tarnished with the Trump name for that matter... It seems you could place a gold "T" on any structure and it immediatly looses any kind of luster... Tacky.

It appears that much of the argument is ranking architect-designed buildings in Manhattan. While I agree that the buildings are ugly, or at best uninspired or wildly inappropriate. Let's look at complete eyesores that are truly ugly. Polish/Slavic credit union in Greenpoint, Brooklyn. I can't find a good enough picture that shows the long side of the building facing McGuinness Blvd. with the weird crests, and giant stone spheres, utility entrance facing the street, weird angles and bizarrely oversized lighting. The pic on their website only shows the side entrance facing the parking lot (?). I would rather look at any of the buildings on this list than having to endure looking at this monstrosity every time i go out. I would have preferred some soviet-era prison-inspired block than this.

Collectively, the ugliest are the new buildings that replaced the old Yorkville which changed a drab but earthy German and Hungarian brownstone community into a modernist glass slum. Much of the blame must go to Mayor Bloomberg who lives in a lovely old townhouse but thinks that over-developed high-rise neighborhoods are just great for other people - and the tax base of the city. Yorkville, where I grew up is a disaster today.

The building across the street from Katz's Deli and next to the builiding housing the Mercury Lounge (217 Houston St). That new 12+ story glass condo is TOTALLY out of place with the surrounding 100+ year old tenement buildings of the Lower East Side.

I thought the LES was a historic district. What were the builders thinking? It's like a tattoo on the Mona Lisa.

How about the new monstrosity on the SW corner of 42nd and 6th Ave where the old Milliken building used to be!

Its a typical glass box, with no set-backs on top or at street level, no fatures and is the typical unimaginative box building looking to completely maximize rental space with no thought for the public or obligation to the city. So bland, so plain, so boxy, so lacking in style for such a key location facing Bryant Park. What a BIG dissapointment we now have to look at for the next 50 years - depressing. Again money with no taste rules the day.

The Tracey Towers!! Completely out of place, ruins the sky line and the buildings look like a prison. I'm sure the building materials and design were chosen with efficiency in mind but the people who live in and the people who drive by it deserve a little better.

@susan: have to agree... the thing with the smoke in union square is awful all around...

As for the Chupi defenders: perhaps my recoil over this building is induced by the fact that i just spent several weeks driving across the country, and if there's one architectural style that's been beaten to death by architects and developers it's Mediterranean (particularly in the Southwest). But, while I'm willing to give El Schnabel points for originality, Chupi is just too look-at-me pink and out of scale for me to find it attractive. Sorry.

As for the Whitney: Needless to say, it is a provocation to put it on this list. But if you really look at it, it does look like a cyclops that gobbles up museum-goers as they enter. It is ugly, in an elegant and interesting way. And while I generally like the building, I sometimes wonder if it wouldn't be better-suited as headquarters for some secret police.

I can see your point on all except for the Whitney #3, though I agree it's not a "pretty" building, it's a beautiful building, because of how it works with the space around it. It creates a beautiful space where it is, in a way that few other buildings in NY do. I LOVE the Whitney ♥.

The Palazzo Chupi is a brilliant monument of creative audacity. It dwarfs and humbles all of the bland glass apartment buildings that have gone up in the area. As the west village grows it should remain a garden of originality, not a transparent warehouse of ad executives and lawyers.

Oh, without a doubt, the AIG building on the West Side Highway. Someone left that cake out in the rain. And hopefully, will never find that recipe again. And sprayed the windows with fake Christmas snow.

There was a lot not to like about Co-op City even before the current garbage strike, but I beg to differ on the architecture.

The apartments are extremely practical for things like views, ventilation, traffic flow, and internal privacy. That wouldn't stop it from being homely, but considering this was a housing project, Herman Jessor did a good job not making it look like one. I particularly like the variations in building style (3 kinds of high-rise), the varying colors of the brickwork, the balconies, and the open porticos at street level that keep the scale from being overwhelming.

I used to stand waiting for the F train on the elevated platform at Fourth Ave. in Brooklyn. My eyes flew across Brooklyn, the East River, Lower Manhattan to those two monstruous towers of the World Trade Center, and I mourned what those ugly disproportionate things had done to the skyline. But, I thought, not much can be done about it. Then I snapped my fingers.

Many of the buildings in this post are not ugly to me, but then again, I like modernist design. There will always be anachronistic folks (like Prince Charles) who love to condemn Modern architecture, and yet I sometimes wonder what cities would look like if these functional and futuristic buildings had not been built. Perhaps, we would have poorly designed and cliche faux Victorian, Georgian, and neo-classical crap which crowd many of the neighborhoods across the East Coast.

Never mind the haters. The Westin is an oasis of fun and charm in the wasteland of modern New York architecture. I'll take it any day over the dozens of blah glass rectangles that pass for new buildings.

As Andrea Lange mentioned on Twitter... I shoulda had some reference to some Fedders monstrosity... And I think I need a separate list for ugly architectural detailing (what's with all the brick townhouses with Italianate balustrades and railings that looks like brass bed posts?)...

@eric: and i like the whitney building. it's likeable ugly -- in a dour-but-elegant old man kind of way. and i do dig Cooper Union...would love to go inside...

May I propose the building at Delancey and Ludlow Streets as a candidate for worst architectural crime in New York? It was built in 2008 and opened in 2009. That is, it seems inspired by the war in Iraq and Afghanistan, or else the designer thought it was worth trying to hide it with camouflage. It also seems ironic that the building is part of the School for Visual Arts!

The NYU dorm on 12th street - 26-story dorm at 110 East 12th Street rising out of St. Ann's.

Curbed: The sad story of the East Village's historic St. Ann's Church, demolished to make way for a controversial 26-story NYU dorm—which left St. Ann's facade in tact like a decapitated head on an invader's planted spear—just got slightly more tragic.

The L Haus, on Venon Blvd. at the foot of the Polaski Br. I walk over the bridge every day and watched it being built. I kept being amazed by the choice of finishes being applied to a luxury building with stunning views of the Newtown Creek (previously home to our nations biggest oil spill) and a water treatment plant (which I would nominate as one of my favorite bits of architecture in NYC, despite the smell). Wow ugly. Like they really put effort into ugly.

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About Gallerina

Carolina A. Miranda is a regular contributor to WNYC and blogs about the arts for the station as "Gallerina." In addition to that, she contributes articles on culture, travel and the arts to a variety of national and regional media, including Time, ArtNews, Travel + Leisure and Budget Travel and Florida Travel + Life. She has reported on the burgeoning industry of skatepark design, architectural pedagogy in Southern California, the presence of street art in museums and Lima's burgeoning food scene, among many other subjects. In 2008, she was named one of eight fellows in the USC Annenberg/Getty Arts Journalism Program for her arts and architecture blog C-Monster.net, which has received mentions in the Wall Street Journal and the New York Times. In January of 2010, the Times named her one of nine people to follow on Twitter. Got a tip? E-mail her at c [@] c-monster [dot] net

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